The Ultimate Side Hustle



How to Manage Your Time and Money

Even if you don’t think of your side hustle as a business, treating it like one will help it succeed. Just like a business, your side hustle needs customers, and you have to define your work and your pay. There may be equipment to maintain, and you have to have revenue goals. Laws and regulations may affect your operations. You have to protect yourself from risk and pay taxes. In this chapter, you’ll learn how to keep your side hustle in the black by managing your time and expenses wisely. Find out how to structure your time. Learn why you need to keep track of your expenses and get ideas for thinking about how to set prices for your products or services or decide what an acceptable wage is. Read about why getting legal advice and buying insurance can protect you from losses due to lawsuits, accident, or injury, and about investments you can make to help you to earn more money.

Your side hustle may be a part-time job on an employer’s payroll, a series of gigs through an on-demand platform, or a freelance business —or you may have multiple side hustles.


Whatever the work and how much of it you do, you need to manage your time and your money to make your side hustle profitable.

Even if you don’t think of your side hustle as a business, it makes sense to treat it like one. To get work, you have to market yourself and your services or products—even if all you do is set up an online profile. Expenses can eat up your earnings if you don’t pay attention to them. In addition, you may need to take steps to protect yourself and your assets in case of an accident, an injury, or a lawsuit.

Consider these aspects of running any business that also pertain to your side hustle:


You are either selling your time, by providing a service, or you are selling a product. Either way, you need to invest some effort in finding people who will pay you. That includes taking the time to craft a professional online profile, including a photo. Independent business owners typically have websites. They may also advertise in local newspapers and online, distribute postcards and flyers, write a blog, or devise other ways to help clients or customers to discover them and learn more about their products or services. For example, an artist, photographer, videographer, or graphic designer will need a portfolio.


Depending on the work, you may need formal contracts with your customers or clients. If you work for an online platform, you agree to its terms and conditions, including the cut it will take of your earnings. Though they obviously vary according to the type of work, contracts will define what you will do, what you have to deliver, how much time you allot, and what your customer owes you. Even a job with a paycheck carries expectations about your work, its quality, your compensation, and your employer’s obligations.


Any of your own equipment you use for your side hustle has to be maintained in good condition, and you need a plan for covering repairs or replacing it when necessary. Many of the jobs in this book require a computer or a smartphone, as well as a reliable broadband Internet connection. You may find you need to upgrade your laptop, phone, Internet, or data service to perform your work successfully.


Whatever you are working toward—paying bills, taking a vacation, buying a new car—you have a target for how much money you want or need to make. Having a budget for your side hustle will enable you to see how much money you need to make—and thus how much you need to work—to cover your materials and any other expenses and still earn enough to reach your goals. If your side hustle is a step toward running your own business full time or gaining experience to change careers, it may be worth it to take a loss temporarily. But without a plan, you won’t know how any decision you make will affect your income.


Some types of work may require you to be licensed or certified, or to comply with health, safety, or business regulations. Side hustles involving driving require a valid driver’s license. If you’re selling baked goods, you are subject to regulations concerning food safety and sanitation. You may need a permit to hold classes in your house, perform, or set up a booth in a public place.


If you are an employee, laws concerning pay, workplace conditions, accident or injury, disability, and liability cover you. But if your side hustle is your own (even if you get your work through an online platform or service), you need measures in place, such as insurance, to shield yourself from losses, medical bills, or legal bills without going bankrupt or losing your house.


Money you earn from self-employment is taxable, but you may be able to deduct your expenses.

Do research, talk to others in your area of work, check with relevant state or local government agencies, and consult qualified professionals for advice and answers to your questions about taxes, licensing, insurance, and the laws that may affect you. The rest of this

chapter offers suggestions for using your time wisely and safeguarding your earnings.


You can devote a lot of time to your side hustle or a little. Your success depends on how you use it.

First, you have to be realistic about the time you have available. If you work in an office full time, it’s likely your side hustle will be limited to evenings and weekends. If you are taking care of family members, you will have to work your side hustle around those responsibilities.

When you know how much time you are able to commit to your side hustle, it’s easier to stay focused on work opportunities that will contribute the most to your financial, career, or personal goals.


Next, you need a schedule. The more control you have over when you work, the more decisive you have to be about doing it. Without a schedule, you may end up not working as much as you need to, or you may take on more than you can manage.

However much you decide to work, you’ll want to take into account when there is demand for what you do. May through October is the busiest period for weddings—important if your side hustle is wedding photographer. If you teach music lessons to middle and high school students, you will probably need weekday afternoons or evenings available during the academic year. If your side hustle is on call, like decorating cakes, you will need to know how much time it takes you to complete an order so you accept only as many as you can realistically deliver.

Although low-skilled on-demand work such as ridesharing, making deliveries, or performing household tasks is available almost anytime through online platforms, the people who make the most money at this work choose regular shifts at times when there is high demand (such as Friday and Saturday nights for ridesharing drivers) and devise strategies for reducing their time waiting between gigs.

While researching on-demand work, Jen Curry at Samaschool did a Postmates delivery that took forty-five minutes and netted her lessthan minimum wage. “You have to know where to position yourself during busy times, take advantage of the bonuses, and stack jobs by picking up and delivering along the same route,” she advises.

For any side hustle in which you are self-employed, you need to ensure you are earning enough to cover the time you spend doing the work. If you already have experience, you will have some idea of how much you should pay yourself; if not, we give you some estimates for what each side hustle in this book typically pays. Take that knowledge and research what people in your community with your expertise usually earn, and you’ll be able to determine a fair rate. Don’t forget to cover your overhead—the expenses you incur to support your business. Time you spend traveling to see clients, packaging up orders, buying supplies, and maintaining your equipment all adds up.


By tracking your time and all of your expenses, you will be able to set prices that cover your costs and may also help to offset any taxes you have to pay on your earnings. If you are losing money to car expenses, equipment, materials, and the IRS, it might make sense for you to try something else.

Beyond what you pay for things such as gasoline, art supplies, and computer software, it may be prudent, depending on your work, to invest in training courses. You may need legal advice, tax advice, and insurance. Even if training isn’t required to operate your side hustle, it may be hard to get hired without it. In addition, having credentials in fields where they’re available may enable you to charge more and attract more customers.

A lawyer can advise you about licensing laws and other regulations you have to comply with, as well as review your contracts to make sure they protect you if clients don’t pay, or if you’re sued. An accountant can advise you about eligible business deductions and help you set aside enough money to pay your taxes. Insurance protects you if you do end up in court, or if you suffer an accident or injury on the job.

Darline Turner began a side hustle as a doula, providing support to women with high-risk pregnancies, after her son was born. At first, she was helping friends, and friends of friends. When she started to get paid, her relationship to her clients and the work had to change: “Especially in birth work, if something goes wrong, everyone present is at fault,” she says. Liability insurance became essential, along with having a properly registered business.

It’s clear why a lot of people resist such expenses: after all, it’s just a side source of income, and the more money you put into it, it seems, the less there is for you at the end of the day. That’s more reason to think carefully about all your costs, and to account for any legal and financial risks, when choosing your side hustle.

Darline became a certified doula and now runs a private practice in Austin. Because many side hustlers envision their work as a test run for a business, or a step toward a new career, the investment in certifications or licenses, or in a new skill that will help you get more work and charge higher rates, will often become worthwhile in the long run. So can buying a piece of equipment or investing in materials to test out a new product design. Some of these investments may be expenses you can deduct from your taxes.

A lot of side hustlers are surprised to learn they owe taxes at all. In fact, earnings of $600 or more from any source have to be reported to the IRS, and if you expect to owe at least $1,000, you may have to pay quarterly estimated taxes.

In 2016, Caroline Bruckner of American University surveyed members of the National Association of the Self-Employed about their income from on-demand and sharing platforms such as Uber, Lyft, and Airbnb. Among those who said they participated, about a third didn’t know they had to make quarterly tax payments on those earnings. Half didn’t know which expenses they could write off or the deductions or credits they were eligible for.

These were people, Bruckner points out, who ran their own businesses and were more likely than the average person to know the rules. They were confused, she concludes, because they did not earn enough to receive a Form 1099, the form that companies use to report payments to independent contractors.

“Once you become aware, you get with the program, file any back taxes owed, and you get organized. Or you’ve already missed so many payments, and what you owe is so overwhelming, that many people walk away and don’t file. I’ve had that analysis confirmed anecdotally by the IRS and CPAs who specialize in advising,” Bruckner says. Meanwhile, some people, though they know they will need to pay taxes, aren’t organized enough managing their expenses and end up in debt when the bills come due.

When you have a handle on all your expenses, you can determine how much you want or need to earn in order to cover your costs and your time, while turning a profit.

Melissa Dinwiddie runs workshops for companies that use games, improvisational theater, and other play-based techniques to teach employees skills that improve communication, collaboration, and managing conflict. It’s a full-time business, and she is a serial entrepreneur. Several of the companies she has run over the past twenty years started as side hustles. “I’ve always thought more in terms of streams of income,” she says. “I haven’t gotten a paycheck since I was twenty-three and worked at a nursery school.”

At first, she thought about pricing in terms of whether she would be paid enough to justify her time. But during one of her early ventures, as a calligrapher making hand-lettered books and artwork, she learned to charge based on how much money she wanted to make from the work. If the customer balked at the price, she would suggest an alternative product rather than cut her rate.

She also learned that customers were not paying her for her time, but for the value of the art she created. “In some cases, I would estimate a book would take twenty hours and it only took me ten, and I would think I should collect less money.” Her epiphany came when delivering to a client who lived in a mansion. “The amount of money was insignificant to her.”

Like Melissa, self-employed side hustlers who sell their products or services independently have control over what they charge. That’s not so much the case for side hustlers who work through online marketplaces and on-demand platforms, which may set your rate for each gig. Even if you are able to set your rate, the platform takes a cut. It may be worth it, if you’re still getting a wage you think is fair

(without costing you) and you would not have the work otherwise because it was too difficult or time consuming to find.

You may make other tradeoffs. Matt, a public school teacher in New Jersey, tutors high school students studying for the SAT. He has tutored privately and worked for test prep centers. Private tutors can charge $75 per hour in his area, but have to find their own clients and put time into creating lesson plans. He earns less when he teaches at the test prep centers, but the work—and thus the income—is more predictable. “The lower wage of the learning center is often made up for by the regularly scheduled work,” he says, and he doesn’t have to deal with cancellations. There are other advantages. With full-time teaching responsibilities in his day job, “It’s a great relief to have lesson plans provided.”

The bottom line: you want your side hustle to succeed on your terms. And for that, you have to be vigilant about your time and your money.

Top Five Industries for Independent Contractors, Consultants, and Freelancers (Percentage of Workers in 2014)

  • Personal Services: 39 percent
  • Construction: 35 percent
  • Agriculture and Mining: 34 percent
  • Finance: 22 percent
  • Professional and Business Services: 22 percent

Source: Aspen Institute, American Action Forum, January 2017

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